ES2660902T3 - Rubber composition with good wet tensile properties and low aromatic oil content - Google Patents

Rubber composition with good wet tensile properties and low aromatic oil content Download PDF

Info

Publication number
ES2660902T3
ES2660902T3 ES06256456.2T ES06256456T ES2660902T3 ES 2660902 T3 ES2660902 T3 ES 2660902T3 ES 06256456 T ES06256456 T ES 06256456T ES 2660902 T3 ES2660902 T3 ES 2660902T3
Authority
ES
Spain
Prior art keywords
functionalized
aromatic oil
rubber composition
oil content
tensile properties
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES06256456.2T
Other languages
Spanish (es)
Inventor
Xiaorong Wang
James E Hall
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bridgestone Corp
Original Assignee
Bridgestone Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bridgestone Corp filed Critical Bridgestone Corp
Application granted granted Critical
Publication of ES2660902T3 publication Critical patent/ES2660902T3/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/04—Monomers containing three or four carbon atoms
    • C08F210/08—Butenes
    • C08F210/10—Isobutene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
    • C08F255/10—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms on to butene polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
    • C08L2666/06—Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T10/00—Road transport of goods or passengers
    • Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
    • Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction 

Abstract

Una composición de caucho para banda de rodadura, que comprende: a. un caucho de dieno; b. una carga funcionalizada que es sílice; y c. un polímero funcionalizado que tiene un bajo peso molecular y el polímero está en un estado líquido a 23° C; en donde dicho polímero funcionalizado interactúa con la carga funcionalizada y es un producto de reacción de un polímero funcionalizado con anhídrido y una amina que tiene la fórmula H2N-(CH2)x-A, en donde x es un número entero que oscila de 0-60 y A es un grupo funcional seleccionado del grupo que consiste en hidroxilo, carboxilo, carbonilo, alcoxi, alcoxicarbonilo, ciano, amino, amido, imido, mercapto, carbamoilo, azido, éster, éter, uretano, peróxido, imidazolilo, piridina, y derivados de los mismos.A rubber tread composition, comprising: a. a diene rubber; b. a functionalized load that is silica; and c. a functionalized polymer having a low molecular weight and the polymer is in a liquid state at 23 ° C; wherein said functionalized polymer interacts with the functionalized charge and is a reaction product of a functionalized polymer with anhydride and an amine having the formula H2N- (CH2) xA, wherein x is an integer ranging from 0-60 and A is a functional group selected from the group consisting of hydroxyl, carboxyl, carbonyl, alkoxy, alkoxycarbonyl, cyano, amino, amido, imido, mercapto, carbamoyl, azido, ester, ether, urethane, peroxide, imidazolyl, pyridine, and derivatives of the same.

Description

imagen1image 1

imagen2image2

imagen3image3

imagen4image4

La práctica de la invención se ilustra con mayor detalle mediante los siguientes ejemplos, que no deben considerarse limitadores del alcance de la invención, como se define en las reivindicaciones. The practice of the invention is illustrated in greater detail by the following examples, which should not be considered as limiting the scope of the invention, as defined in the claims.

Ejemplos Examples

Ejemplo 1: Preparación de poliisobutileno imida Example 1: Preparation of polyisobutylene imide

5 211 g de anhídrido poliisobutenil-succínico (Mw: 1900; Mn: 1000; 95 meq de COOH/100 g; adquirido en Chevron Chemicals con el nombre comercial OLOA 15500) y 10,24 g de 3-(dimetilamino)propilamina (adquirido de Aldrich) se cargaron en un frasco seco de 1,5 L. Los dos materiales se mezclaron enérgicamente durante una hora. La temperatura de la mezcla aumentó de 23°C a 65°C , indicando que se ha producido una reacción química. Una vez completada la reacción, se dejó enfriar la composición a temperatura ambiente durante 4 horas. Entonces se 5 211 g of polyisobutenyl succinic anhydride (Mw: 1900; Mn: 1000; 95 meq of COOH / 100 g; purchased from Chevron Chemicals under the trade name OLOA 15500) and 10.24 g of 3- (dimethylamino) propylamine (purchased from Aldrich) were loaded into a dry 1.5L bottle. The two materials were mixed vigorously for one hour. The temperature of the mixture increased from 23 ° C to 65 ° C, indicating that a chemical reaction has occurred. After completion of the reaction, the composition was allowed to cool to room temperature for 4 hours. Then

10 colocó la composición en un horno de vacío a 110°C durante 20 horas para deshidratar la composición. Se observó el producto final como un líquido viscoso parduzco. El ensayo mediante análisis del espectro infrarrojo confirmó que el producto final era polibutileno imida. 10 placed the composition in a vacuum oven at 110 ° C for 20 hours to dehydrate the composition. The final product was observed as a brownish viscous liquid. The test by infrared spectrum analysis confirmed that the final product was polybutylene imide.

Ejemplo 2 (Ejemplo comparativo) Example 2 (Comparative Example)

Los siguientes componentes se mezclaron en un mezclador Brabender de 300 g a una velocidad de agitación de 15 60 rpm, con una temperatura inicial de 110°C . Las cantidades indicadas están basadas en 100 partes de caucho. The following components were mixed in a 300 g Brabender mixer at a stirring speed of 15 60 rpm, with an initial temperature of 110 ° C. The amounts indicated are based on 100 parts of rubber.

Componente Component
Cantidad Quantity

Caucho de estireno-butadieno1 Styrene-Butadiene Rubber1
100 100

Carga de sílice precipitada2 Precipitated silica charge2
70,0 70.0

Aceite aromático3 Aromatic oil3
30,0 30.0

Cera de parafina4 Paraffin Wax4
1,50 1.50

Ácido esteárico5 Stearic Acid5
2,00 2.00

Santoflex 13 (antioxidante)6 Santoflex 13 (antioxidant) 6
0,95 0.95

Si 69 (Agente de acoplamiento de silano)7 Yes 69 (Silane Coupling Agent) 7
8,00 8.00

1. 23,5% estireno, solución polimerizada, viscosidad de Mooney a 100°C = 55, 11% contenido de vinilo; disponible en Firestone Synthetic (Akron, OH) 2. Adquirido en PPG (Pittsburgh, PA, EE. UU.) como sílice amorfa hidratada 3. Adquirido en Mobil (Fairfax, VA, EE. UU.) con el nombre comercial Mobilsol 90 4. Adquirido en Aston Wax Corp. (Tilusville, PA, EE. UU.) 5. Adquirido en Sherex Chemical (Dublín, OH, EE. UU.) 6. Nombre químico: N-(1,3-dimetilbutiI)-N'-fenil-P-fenilen-diamina; adquirido en Monsanto (St. Louis, MO) con el nombre comercial 6PPD 7. Nombre químico: tetrasulfuro de bis-(3-trietoxi-silil propilo); adquirido en Degussa (Parsippany, NJ) 1. 23.5% styrene, polymerized solution, Mooney viscosity at 100 ° C = 55, 11% vinyl content; available in Firestone Synthetic (Akron, OH) 2. Acquired in PPG (Pittsburgh, PA, USA) as hydrated amorphous silica 3. Acquired in Mobil (Fairfax, VA, USA) under the trade name Mobilsol 90 4 Acquired from Aston Wax Corp. (Tilusville, PA, USA) 5. Acquired from Sherex Chemical (Dublin, OH, USA) 6. Chemical name: N- (1,3-dimethylbutiI) -N ' -phenyl-P-phenylene diamine; acquired in Monsanto (St. Louis, MO) under the trade name 6PPD 7. Chemical name: bis- (3-triethoxy-silyl propyl) tetrasulfide; acquired in Degussa (Parsippany, NJ)

Etapa de mezcla maestra: En el tiempo cero, el caucho de estireno-butadieno se cargó en el mezclador y se calentó a una temperatura inicial de 110°C. Los componentes restantes se añadieron en t=0,5 min. La mezcla se vertió en t=5 min, cuando la temperatura del concentrado se aproximó a unos 160°C. Master mixing stage: At zero time, styrene-butadiene rubber was loaded into the mixer and heated to an initial temperature of 110 ° C. The remaining components were added in t = 0.5 min. The mixture was poured in t = 5 min, when the temperature of the concentrate approached about 160 ° C.

Etapa de remolienda: El concentrado de la mezcla maestra se remolió esencialmente a las mismas condiciones que 20 la mezcla maestra. La etapa de remolienda se usó para mejorar la mezcla entre el polímero y las cargas. Towing stage: The concentrate of the master mix was essentially towed under the same conditions as the master mix. The towing stage was used to improve the mixture between the polymer and the charges.

Los siguientes componentes se añadieron a los componentes mezclados en las etapas de la mezcla maestra y de remolienda. Los componentes se mezclaron en el mezclador Brabender de 300 g a una velocidad de agitación de 60 rpm, con una temperatura inicial de 75°C. Las cantidades están basadas en 100 partes de caucho. The following components were added to the mixed components in the master and mold mixing stages. The components were mixed in the 300 g Brabender mixer at a stirring speed of 60 rpm, with an initial temperature of 75 ° C. The quantities are based on 100 parts of rubber.

Componente Component
Cantidad Quantity

Azufre1 Sulfur1
1,70 1.70

N-(ciclohexiltio)ftalimida (retardador)2 N- (cyclohexylthio) phthalimide (retarder) 2
0,25 0.25

Óxido de cinc3 Zinc Oxide3
2,50 2.50

6 6

Componente Component
Cantidad Quantity

Ciclohexil-benzotiazol sulfonamida (acelerador)4 Cyclohexyl-benzothiazole sulfonamide (accelerator) 4
1,50 1.50

Difenillguanidina5 Diphenylguanidine5
0,50 0.50

1. Adquirido en International Sulphur (Mt. Pleasant, TX, EE. UU.) 2. Adquirido en Monsanto (St. Louis, MO, EE. UU.) con el nombre comercial Santogard PVI 3. Adquirido en Zinc Corp. America (Monaca, PA, EE. UU.) 4. Adquirido en Monsanto (St. Louis, MO, EE. UU.) 5. Adquirido en Monsanto (St. Louis, MO, EE. UU.) 1. Acquired at International Sulfur (Mt. Pleasant, TX, USA) 2. Acquired in Monsanto (St. Louis, MO, USA) under the trade name Santogard PVI 3. Acquired at Zinc Corp. America ( Monaca, PA, USA) 4. Acquired in Monsanto (St. Louis, MO, USA) 5. Acquired in Monsanto (St. Louis, MO, USA)

Etapa de mezcla final: En el tiempo cero, el concentrado de mezcla maestra se añadió a la mezcladora, donde se mantuvo la temperatura a 75°C. Entonces se cargaron los componentes en t=0,5 min. La mezcla final se vertió en t=1,3 minutos cuando la temperatura del concentrado alcanzaba aproximadamente 90°C . Final mixing stage: At zero time, the master mix concentrate was added to the mixer, where the temperature was maintained at 75 ° C. The components were then loaded at t = 0.5 min. The final mixture was poured in t = 1.3 minutes when the temperature of the concentrate reached approximately 90 ° C.

Ejemplo 3: Sustitución parcial del aceite aromático Example 3: Partial replacement of aromatic oil

5 La composición de caucho del Ejemplo 2 se preparó usando los mismos componentes y el mismo procedimiento, salvo que se sustituyeron solo 15 partes de aceite aromático con 15 partes de poliisobutileno imida preparado en el Ejemplo 1. Ejemplo 4: Sustitución total de aceite aromático La composición de caucho del Ejemplo 2 se preparó usando los mismos componentes y el mismo procedimiento, salvo The rubber composition of Example 2 was prepared using the same components and the same procedure, except that only 15 parts of aromatic oil were replaced with 15 parts of polyisobutylene imide prepared in Example 1. Example 4: Total replacement of aromatic oil Rubber composition of Example 2 was prepared using the same components and the same procedure, except

que se sustituyeron las 30 partes de aceite aromático con 30 partes de poliisobutileno imida preparado en el Ejemplo 1. 10 La Tabla 1 resume los resultados de los experimentos de los Ejemplos 2-4: The 30 parts of aromatic oil were replaced with 30 parts of polyisobutylene imide prepared in Example 1. 10 Table 1 summarizes the results of the experiments in Examples 2-4:

Tabla 1: Ejemplos de análisis 2-4 Table 1: Examples of analysis 2-4

Componentes Components
Ejemplo 2 Ejemplo 3 Ejemplo 4 Example 2 Example 3 Example 4

Caucho de estireno-butadieno (20% St) Styrene-Butadiene Rubber (20% St)
100 100 100 100 100 100

Sílice precipitada Precipitated silica
70 70 70 70 70 70

Aceite aromático Aromatic oil
30 15 0 30 fifteen 0

Poliisobutileno imida Polyisobutylene imide
0 15 30 0 fifteen 30

Azufre Sulfur
1,7 1,7 1,7 1.7 1.7 1.7

Ensayos essays

Viscosidad de Mooney a 130°C Mooney viscosity at 130 ° C
57,7 56,1 55,3 57.7 56.1 55.3

Índice de dispersión de negro de carbón Carbon black dispersion index
98,5 98,9 97,1 98.5 98.9 97.1

Shore A a 22°C (3 s) Shore A at 22 ° C (3 s)
57,5 63,1 64,0 57.5 63.1 64.0

a 100°C (3 s) at 100 ° C (3 s)
52,2 57,3 58,1 52.2 57.3 58.1

Tracción circunferencial a 23°C Circumferential traction at 23 ° C

Tb (MPa) Tb (MPa)
17,29 15,45 15,07 17.29 15.45 15.07

Eb (%) Eb (%)
610,2 544,1 523,4 610.2 544.1 523.4

M300 M300
6,36 6,31 6,82 6.36 6.31 6.82

M50 M50
0,98 1,01 1,16 0.98 1.01 1.16

Resistencia al desgarramiento (kN/m) Tear Resistance (kN / m)
20,9 21,1 19,0 20.9 21.1 19.0

Propagación del desgarramiento circunferencial (%) 170°C Propagation of circumferential tearing (%) 170 ° C
398 402 373 398 402 373

Tg del compuesto (tan δ) Tg of compound (tan δ)
-39,2 -39,7 -43,1 -39.2 -39.7 -43.1

Medidor británico portátil de deslizamiento en hormigón húmedo Portable British wet concrete sliding meter
63 69 67 63 69 67

tan δ a 50°C tan δ at 50 ° C
0,13322 0,11833 0,11204 0.13322 0,11833 0.11204

7 7

imagen5image5

Claims (1)

imagen1image 1 imagen2image2
ES06256456.2T 2005-12-28 2006-12-19 Rubber composition with good wet tensile properties and low aromatic oil content Active ES2660902T3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US75438905P 2005-12-28 2005-12-28
US754389P 2005-12-28

Publications (1)

Publication Number Publication Date
ES2660902T3 true ES2660902T3 (en) 2018-03-26

Family

ID=37872475

Family Applications (1)

Application Number Title Priority Date Filing Date
ES06256456.2T Active ES2660902T3 (en) 2005-12-28 2006-12-19 Rubber composition with good wet tensile properties and low aromatic oil content

Country Status (6)

Country Link
US (1) US9752020B2 (en)
EP (1) EP1803771B1 (en)
JP (1) JP5196783B2 (en)
CN (1) CN1995119B (en)
BR (1) BRPI0605395A (en)
ES (1) ES2660902T3 (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2660902T3 (en) 2005-12-28 2018-03-26 Bridgestone Corporation Rubber composition with good wet tensile properties and low aromatic oil content
FR2925061B1 (en) * 2007-12-18 2010-01-15 Michelin Soc Tech RUBBER COMPOSITION, IN PARTICULAR FOR THE MANUFACTURE OF TIRES
FR2925062B1 (en) * 2007-12-18 2011-03-04 Michelin Soc Tech RUBBER COMPOSITION, IN PARTICULAR FOR THE MANUFACTURE OF TIRES
FR2925388A1 (en) * 2007-12-21 2009-06-26 Michelin Soc Tech DEVICE AND METHOD FOR PREPARING A PROFILE OF ELASTOMERIC THERMOPLASTIC GEL
KR101596953B1 (en) 2007-12-31 2016-02-23 가부시키가이샤 브리지스톤 Metal Soaps Incorporated in Rubber Compositions and Method for Incorporating Such Soaps in Rubber Compositions
US9062189B2 (en) * 2008-01-18 2015-06-23 Exxonmobil Chemical Patents Inc. Elastomeric compositions comprising hydrocarbon polymer additives
CN102131856B (en) * 2008-06-26 2014-03-05 株式会社普利司通 Rubber compositions including metal-functionalized polyisobutylene derivatives and methods for preparing such compositions
US7906592B2 (en) * 2008-07-03 2011-03-15 Bridgestone Corporation Polymers functionalized with imide compounds containing a protected amino group
JP5438132B2 (en) 2009-01-23 2014-03-12 株式会社ブリヂストン Polymers functionalized with polycyano compounds
ES2465070T3 (en) 2009-01-23 2014-06-05 Bridgestone Corporation Polymers functionalized with nitrile compounds containing a protected amino group
US8389609B2 (en) 2009-07-01 2013-03-05 Bridgestone Corporation Multiple-acid-derived metal soaps incorporated in rubber compositions and method for incorporating such soaps in rubber compositions
US20110054069A1 (en) * 2009-08-28 2011-03-03 Bridgestone Corporation Rubber composition having improved crack resistance
US8450409B2 (en) 2009-08-28 2013-05-28 Bridgestone Corporation Method for mixing a rubber composition
US9803060B2 (en) 2009-09-10 2017-10-31 Bridgestone Corporation Compositions and method for making hollow nanoparticles from metal soaps
US8338544B2 (en) * 2009-12-21 2012-12-25 Bridgestone Corporation Polymers functionalized with polyoxime compounds and methods for their manufacture
WO2012050657A1 (en) 2010-10-13 2012-04-19 Exxonmobil Chemical Patents Inc. Hydrocarbon polymer modifiers for elastomeric compositions
EP2630190B1 (en) 2010-10-18 2018-08-22 Bridgestone Corporation Tread rubber compounds having improved abrasion resistance using functionalized liquid polybutadiene
US8748531B2 (en) 2010-12-10 2014-06-10 Bridgestone Corporation Polymers functionalized with oxime compounds containing an acyl group
US8802755B2 (en) 2011-01-18 2014-08-12 Bridgestone Corporation Rubber compositions including metal phosphate esters
US8962766B2 (en) 2011-09-15 2015-02-24 Bridgestone Corporation Polymers functionalized with polyhydrazone compounds
CN103450524B (en) * 2012-06-01 2015-04-22 建大橡胶（中国）有限公司 Formula and preparation method of snow tire
CN104995248B (en) 2012-11-02 2017-12-08 株式会社普利司通 Rubber composition and its preparation method comprising metal carboxylate
US9822245B2 (en) 2013-03-27 2017-11-21 Sumitomo Rubber Industries, Ltd. Studless winter tire
JP6084911B2 (en) 2013-09-10 2017-02-22 住友ゴム工業株式会社 Pneumatic tire
KR102138567B1 (en) 2014-04-11 2020-07-28 한온시스템 주식회사 Method of controlling compressor and compressor
JP6519237B2 (en) * 2015-03-10 2019-05-29 横浜ゴム株式会社 Rubber composition and pneumatic tire using the same
EP3694896B1 (en) 2017-10-14 2024-01-10 TPC Group LLC Non-random isobutylene copolymers
KR102475296B1 (en) * 2020-07-21 2022-12-06 디엘케미칼 주식회사 Modified polybutene elastomers for rubber composition and thereof

Family Cites Families (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248643B (en) * 1959-03-30 1967-08-31 The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) Process for the preparation of oil-soluble aylated amines
NL124842C (en) * 1959-08-24
NL255193A (en) * 1959-08-24
NL124306C (en) * 1959-08-24
US3223495A (en) * 1961-09-11 1965-12-14 Exxon Research Engineering Co Motor fuel composition
DK127733C (en) * 1965-01-08 1974-05-27 Strol Ltd Sludge dispersing additive.
US3443918A (en) * 1965-09-21 1969-05-13 Chevron Res Gasoline composition
US3461108A (en) * 1965-10-14 1969-08-12 Gulf Research Development Co Process of forming copolymers of maleic anhydride and an aliphatic olefin having six carbon atoms
US3272746A (en) * 1965-11-22 1966-09-13 Lubrizol Corp Lubricating composition containing an acylated nitrogen compound
US3580893A (en) * 1966-10-25 1971-05-25 Gulf Research Development Co Process for the preparation of cyclic acid anhydrides
US3706704A (en) * 1966-10-25 1972-12-19 Gulf Research Development Co Preparation of c6-c10 olefin-maleic anhydride copolymers
US3560456A (en) * 1969-05-26 1971-02-02 Gulf Research Development Co Process of forming copolymers of maleic anhydride and an aliphatic olefin having from 16 to 18 carbon atoms
US3560457A (en) * 1969-05-26 1971-02-02 Gulf Research Development Co Process of forming copolymers of maleic anhydride and an aliphatic olefin having from 12 to 14 carbon atoms
US3560455A (en) * 1969-05-26 1971-02-02 Gulf Research Development Co Process of forming copolymers of maleic anhydride and an aliphatic olefin having from 20 to 30 carbon atoms
US3729450A (en) * 1971-03-10 1973-04-24 Gulf Research Development Co Method of recovering copolymers
US3836511A (en) * 1971-03-12 1974-09-17 Exxon Research Engineering Co Process for sulfonating unsaturated elastomers
US3944552A (en) * 1972-06-26 1976-03-16 The Goodyear Tire & Rubber Company N,N'-bisimidothio-diamines
US3729451A (en) * 1972-07-10 1973-04-24 Gulf Research Development Co Process for copolymerization of maleic anhydride with 1-olefins
US3912764A (en) * 1972-09-29 1975-10-14 Cooper Edwin Inc Preparation of alkenyl succinic anhydrides
DE2702604C2 (en) * 1977-01-22 1984-08-30 Basf Ag, 6700 Ludwigshafen Polyisobutenes
US4410437A (en) * 1978-12-04 1983-10-18 Chevron Research Company Amine substituted hydrocarbon polymer dispersant lubricating oil additives
US4234435A (en) * 1979-02-23 1980-11-18 The Lubrizol Corporation Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation
FR2472000A1 (en) * 1979-12-20 1981-06-26 Rhone Poulenc Ind PROCESS FOR IMPROVING COMPATIBILITY OF PLASTIFIERS AND LOADS IN POLYMERS
JPS57195105A (en) * 1981-05-26 1982-11-30 Kuraray Co Ltd Preparation of modified cis-1,4-polyisoprene rubber
JPS58113233A (en) * 1981-12-28 1983-07-06 Nippon Zeon Co Ltd Deterioration-resistant rubber member
JPS598737A (en) * 1982-07-06 1984-01-18 Kuraray Co Ltd Rubber composition
EP0178752A1 (en) * 1984-09-14 1986-04-23 Cameron Iron Works, Inc. Liquid rubber-toughened elastomer
GB8818711D0 (en) 1988-08-05 1988-09-07 Shell Int Research Lubricating oil dispersants
US5112507A (en) * 1988-09-29 1992-05-12 Chevron Research And Technology Company Polymeric dispersants having alternating polyalkylene and succinic groups
US5175225A (en) * 1989-09-29 1992-12-29 Chevron Research And Technology Company Process for preparing polymeric dispersants having alternating polyalkylene and succinic groups
US5137978A (en) * 1990-05-17 1992-08-11 Ethyl Petroleum Additives, Inc. Substituted acylating agents and their production
US5137980A (en) * 1990-05-17 1992-08-11 Ethyl Petroleum Additives, Inc. Ashless dispersants formed from substituted acylating agents and their production and use
US5150754A (en) * 1991-05-28 1992-09-29 Mobil Oil Corporation Aqueous and petroleum gel method for preventing water-influx
WO1993006194A1 (en) * 1991-09-13 1993-04-01 Chevron Research And Technology Company Fuel additive compositions containing polyisobutenyl succinimides
TW242630B (en) 1991-11-15 1995-03-11 Shell Internat Res Schappej B V
US5625004A (en) * 1992-07-23 1997-04-29 Chevron Research And Technology Company Two-step thermal process for the preparation of alkenyl succinic anhydride
US5319030A (en) * 1992-07-23 1994-06-07 Chevron Research And Technology Company One-step process for the preparation of alkenyl succinic anhydride
US5286799A (en) * 1992-07-23 1994-02-15 Chevron Research And Technology Company Two-step free radical catalyzed process for the preparation of alkenyl succinic anhydride
GB9226108D0 (en) * 1992-12-15 1993-02-10 Bp Chem Int Ltd Resin-free succinimides
JP3001385B2 (en) * 1993-12-13 2000-01-24 シェブロン ケミカル カンパニー Polymer dispersant
CN1091765A (en) * 1994-01-18 1994-09-07 吉林省华详实业公司 Polyurethane binder/sealant and making method
GB9511266D0 (en) * 1995-06-05 1995-08-02 Exxon Chemical Patents Inc Ester-free synthetic lubricating oils
DE19603529A1 (en) * 1996-02-01 1997-08-07 Bosch Gmbh Robert Car headlamp
US5777025A (en) * 1996-02-09 1998-07-07 Exxon Chemical Patents Inc. Process for preparing polyalkenyl substituted C4 to C10 dicarboxylic acid producing materials
US5792729A (en) * 1996-08-20 1998-08-11 Chevron Chemical Corporation Dispersant terpolymers
JP3612160B2 (en) * 1997-01-08 2005-01-19 住友ゴム工業株式会社 Pneumatic tire
US5916961A (en) * 1997-07-11 1999-06-29 Bridgestone Corporation Amine-initiated elastomers having hysteresis reducing interaction with silica
US5981662A (en) * 1997-09-16 1999-11-09 The Goodyear Tire & Rubber Company Rubber compounds containing polymeric bis-succinimide polysulfides
US5972853A (en) 1997-11-12 1999-10-26 Exxon Chemical Patents Inc. Wear control with dispersants employing poly alpha-olefin polymers
US5922792A (en) * 1998-01-13 1999-07-13 The Goodyear Tire & Rubber Company Rubber compounds containing a sulfur containing bis-succinimide
US6204354B1 (en) 1998-05-06 2001-03-20 Bridgestone Corporation Soft compounds derived from polypropylene grafted disubstituted ethylene- maleimide copolymers
US6207763B1 (en) * 1998-06-12 2001-03-27 Bridgestone Corporation Application of disubstituted ethylene-maleimide copolymers in rubber compounds
US6372855B1 (en) * 1998-08-31 2002-04-16 The Yokohama Rubber Co., Ltd. Polymer containing isobutylene as repeating unit and rubber composition containing the same
US6133354A (en) * 1998-11-17 2000-10-17 Bridgestone Corporation Copolymers as additives in thermoplastic elastomer gels
JP2000273240A (en) * 1999-03-29 2000-10-03 Idemitsu Atochem Kk Rubber composition for tire tread
JP4958364B2 (en) * 2000-03-23 2012-06-20 株式会社ブリヂストン Method for forming a mold polymer gel
US6350800B1 (en) * 2000-06-05 2002-02-26 Bridgestone Corporation Soft polymer gel
US6384134B1 (en) * 2000-06-05 2002-05-07 Bridgestone Corporation Poly(alkenyl-co-maleimide) and maleated polyalkylene grafted with grafting agent, and epoxy polymer
US6417259B1 (en) * 2000-06-05 2002-07-09 Bridgestone Corporation Polyalkylene grafted centipede polymers
US6353054B1 (en) * 2000-07-31 2002-03-05 Bridgestone Corporation Alkenyl-co-maleimide/diene rubber copolymers and applications
US6359064B1 (en) * 2000-09-08 2002-03-19 Bridgestone Corporation Compound of polyester and polyalkylene grafted comb polymer
US6458881B1 (en) * 2000-11-20 2002-10-01 Bridgestone Corporation Soft polymeric compounds including hydrophobic fillers
US20020188064A1 (en) * 2001-05-22 2002-12-12 Bridgestone/Firestone Research, Inc. Centipede ionomers
US6403724B1 (en) * 2001-06-04 2002-06-11 Bridgestone Corporation Polymer gel including dendrimers
DE50109350D1 (en) * 2001-06-29 2006-05-18 Continental Ag Rubber compound for treads of tires
US6401776B1 (en) * 2001-08-14 2002-06-11 Bridgestone Corporation Thermoplastic elastomers and method of making the same
US6632781B2 (en) * 2001-09-28 2003-10-14 Chevron Oronite Company Llc Lubricant composition comprising alkali metal borate dispersed in a polyalkylene succinic anhydride and a metal salt of a polyisobutenyl sulfonate
US6845797B2 (en) * 2001-10-12 2005-01-25 Bridgestone Corporation Tire compositions comprising epoxidized natural rubber and a functionalized polyolefin
US6699813B2 (en) * 2001-11-07 2004-03-02 Bridgestone Corporation Lanthanide-based catalyst composition for the manufacture of polydienes
US6706823B2 (en) * 2001-12-31 2004-03-16 Bridgestone Corporation Conductive gels
US20030130398A1 (en) * 2001-12-31 2003-07-10 Bridgestone Corporation Soft polymeric compounds including metal oxide fillers
JP4683928B2 (en) 2002-12-18 2011-05-18 株式会社ブリヂストン Clay exfoliation method, composition obtained from the method, and modified rubber containing the composition
US7141622B2 (en) * 2003-07-30 2006-11-28 The Goodyear Tire & Rubber Company Process for preparing a silica/rubber blend which includes dispersing silica, asilica coupling agent, and a low molecular weight end-group functionalized diene rubber throughout a cement of a conventional rubbery polymer, and subsequently recovering the silica/rubber blend from an organic solvent
EP1535959B1 (en) * 2003-11-28 2012-09-05 Sumitomo Rubber Industries, Ltd. Rubber composition for a tire and tire using the same
DE602005020997D1 (en) 2005-12-16 2010-06-10 Exxonmobil Chem Patents Inc PROCESSING AGENT FOR ELASTOMER COMPOSITIONS
ES2660902T3 (en) 2005-12-28 2018-03-26 Bridgestone Corporation Rubber composition with good wet tensile properties and low aromatic oil content
US7700673B2 (en) * 2006-12-22 2010-04-20 Bridgestone Corporation Reduced oil rubber compositions including N-substituted polyalkylene succinimide derivates and methods for preparing such compositions

Also Published As

Publication number Publication date
CN1995119B (en) 2012-07-04
EP1803771B1 (en) 2017-12-06
US20070149689A1 (en) 2007-06-28
US9752020B2 (en) 2017-09-05
JP2007182572A (en) 2007-07-19
JP5196783B2 (en) 2013-05-15
BRPI0605395A (en) 2007-10-16
EP1803771A1 (en) 2007-07-04
CN1995119A (en) 2007-07-11

Similar Documents

Publication Publication Date Title
ES2660902T3 (en) Rubber composition with good wet tensile properties and low aromatic oil content
Shi et al. Hindered phenol grafted carbon nanotubes for enhanced thermal oxidative stability of polyethylene
ES2334702T3 (en) PREPARATION PROCEDURE FOR A TIRE WITH IMPROVED SILICON EFFORT.
ES2334510T3 (en) MANUFACTURING PROCEDURE OF A TIRE COMPOSITION WITH IMPROVED SILICON REINFORCEMENT.
CN107429005B (en) Rubber composition and pneumatic tire
CN105934473B (en) Rubber composition and pneumatic tire
KR102253249B1 (en) Functionalized polymer composition
BRPI0901601A2 (en) functionalized elastomers
ES2290098T3 (en) RUBBER COMPOSITION.
BRPI0903440A2 (en) method for improving cold-flow resistance of polymers
JP2013163759A (en) Rubber composition for tire and pneumatic tire
US10100133B2 (en) Process for functionalising polymers
ES2659380T3 (en) Cyclic carbonate azide
US10093762B2 (en) Process for modifying polymers
RU2235740C2 (en) Rubber compound
JPH0411501A (en) Pneumatic tire
JP2020050708A (en) Bale of conjugated diene polymer composition and method for producing the same
CN107849159B (en) Polymer-modified manufacturing method, polymer-modified, rubber composition and pneumatic tire
RU2177969C1 (en) Bitumen-polymer composition production
JP6242720B2 (en) Rubber composition for tire and pneumatic tire
JP6242719B2 (en) Rubber composition for tire and pneumatic tire
JP2011530625A (en) Non-agglomerated styrene-butadiene diblock copolymer-containing blend and method of manufacture
RU2235741C2 (en) Rubber compound
JP7427438B2 (en) Modified natural rubber, rubber composition using the same, and pneumatic tire using the same
WO2020105371A1 (en) Modified natural rubber, rubber composition using same, and method for producing modified natural rubber